American Chemical Society
ol900118d_si_001.pdf (7.21 MB)

Synthesis of Aminocyclobutanes through Ring Expansion of N-Vinyl-β-Lactams

Download (7.21 MB)
journal contribution
posted on 2009-03-19, 00:00 authored by Lawrence L. W. Cheung, Andrei K. Yudin
Both eight-membered enamide rings and fused [4.2.0]aminocyclobutane-containing δ-lactams can be accessed from N-vinyl-β-lactams. The eight-membered rings are made through a [3,3] sigmatropic rearrangement. At elevated temperature, the eight-membered lactam undergoes electrocyclization to furnish fused cyclobutane δ-lactams in a diastereoselective manner.